The discovery of an enantioselective receptor for (-)-adenosine from a racemic dynamic combinatorial library

Journal of the American Chemical Society

Volumn 128, Issue 38, 2006, Pages 12422-12423

  Voshell, Sharon M ^b   Lee, Stephen J ^a   Gagné, Michel R ^b  

^a U S ARMY RESEARCH OFFICE   (United States)

^b University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE RECEPTOR;

ARTICLE; CHEMICAL BINDING; COMBINATORIAL LIBRARY; ENANTIOMER; ENANTIOSELECTIVITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POLARIMETRY; ULTRAVIOLET SPECTROSCOPY;

ADENOSINE; COMBINATORIAL CHEMISTRY TECHNIQUES; DIPEPTIDES; HYDRAZONES; PROLINE; RECEPTORS, PURINERGIC P1; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 33749176806     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0647699     Document Type: Article

References (24)

1. For reviews, see: (a) Ramström, O.; Lehn, J.-M. Nat. Rev. Drug Discovery 2002, 1, 26-36.
2. (b) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952.
3. (c) Otto, S.; Furlan, R. L. E.; Sander, J. K. M. Drug Discovery Today 2002, 7, 117-125.
4. (d) See also: Zhang, W.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 4416-4439.
5. Lam, R. T. S.; Belenguer, A.; Roberts, S. L.; Naumann, C.; Jarrosson, T.; Otto, S.; Sanders, J. K. M. Science 2005, 308, 667-669.
6. (a) González-Álvarez, A.; Alfonso, I.; Gotor, V. Chem. Commun. 2006 2224-2226.
7. (b) Corbett, P. T.; Tong, L. H.; Sander, J. K. M.; Otto, S. J. Am. Chem. Soc. 2005, 127, 8902-8903.
8. For the use of chiral receptors for enantioselective binding of amines, see: (a) Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313-3361.
9. (b) Naemura, K.; Tobe, Y.; Kaneda, T. Coord. Chem. Rev. 1996, 148, 199-219.
10. (c) Stoddart, J. F. Top. Stereochem. 1987, 17, 207-288.
11. Amide-based receptors incorporating π-stacking and H-bond donor/acceptor moieties bind nucleobases, though enantio-recognition must necessarily come from the sugar portion of the analyte. See for example: (a) Conn, M. M.; Deslongchamps, G.; de Mendoza, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548-3557.
12. (b) Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561-6562.
13. Adenosine nucleotide receptors are ubiquitous and important medicinal targets, influencing such conditions as hypertension, inflammation, asthma, memory, immune responses, etc. See for example: Jacobson, K. A.; Gao, Z.-G. Nat. Rev. Drug Discovery 1996, 5, 247-264.
14. Concentrating a single enantiomer into the amplified receptor causes a concomitant buildup of its mirror image into the other members of the DCL. This effect reduces the LP signal from these enantioenriched components and dilutes the entropic cost of deracemization.
15. (a) Goodall, D. M. Trends Anal. Chem. 1993, 12, 177-184.
16. (b) Bobbitt, D. R.; Linder, S. W. Trends Anal. Chem. 2001, 20, 111-123.
17. (c) Halls, S. C.; Lewis, N. G. Tetrahedron: Asymmetry 2003, 14, 649-658.
18. Roberts, S. L.; Furlan, R. L. E.; Otto, S.; Sanders, J. K. M. Org. Biomol. Chem. 2003, 1, 1625-1633.
19. (S,S)-2 gives a levorotatory (negative phase) peak in the LP (Figure 1d).
20. This analysis accounts for statistical quantities of the achiral heterodimer, but may not account for templating induced changes in its concentration.
21. Cyclic peptides selectively bind chiral quaternary ammonium ions. See: (a) Heinrichs, G.; Vial, L.; Lacour, J.; Kubik, S. Chem. Commun. 2003, 1252-1253.
22. For achiral binding, see: (b) Madison, V.; Deber, C. M.; Blout, E. R. J. Am. Chem. Soc. 1977, 99, 4788-4798 and references therein.
23. The ratio of (R,R)-2 to (S,S)-2 was not exactly 1:1 in the pseudo-racemate.
24. Direct characterization of the differential binding properties of 2 and (-)-adenosine was hindered by poor solubility in nonacidic templating solutions (where library exchange does not occur), perhaps reasonably suggesting that the actual analyte is protonated. See: Kampf, G.; Kapinos, L. E.; Griesser, R.; Lippert, B.; Sigel, H. J. Chem. Soc., Perkin Trans. 2 2002, 1320-1327.